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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 20:06:08 UTC
Update Date2022-03-07 02:54:23 UTC
HMDB IDHMDB0035155
Secondary Accession Numbers
  • HMDB35155
Metabolite Identification
Common Namebeta-Geraniol
Descriptionbeta-Geraniol, also known as (E)-nerol, the isomer of nerol (or geranyl alcohol, is a monoterpenoid alcohol. It belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. beta-Geraniol is an isoprenoid lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. beta-Geraniol has a sweet, citrus, and floral taste. beta-Geraniol is found in highest concentrations in common grapes, black walnuts, and common thymes and in lower concentrations in cardamoms, common oregano, and gingers. beta-Geraniol has also been detected in lemon verbena, oval-leaf huckleberries, common pea, sweet cherries, and nopals. This could make beta-geraniol a potential biomarker for the consumption of these foods. It is found in as an alcohol and as its ester in many essential oils including geranium oil. It is the primary part of rose oil, palmarosa oil, and citronella oil (Java type) and occurs in small quantities in geranium, lemon, and many other essential oils. Geraniol is a monoterpenoid and an alcohol found in cannabis plants (PMID:6991645 ). Because it has a rose-like odor, it is commonly used in perfumes. It is used to create flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. Geraniol is produced by the scent glands of honeybees to mark nectar-bearing flowers and locate the entrances to their hives (http//doi:10.1051/apido:19900403).
Structure
Data?1563862674
Synonyms
ValueSource
(2E)-3,7-Dimethyl-2,6-octadien-1-olChEBI
(2E)-GeraniolChEBI
(e)-3,7-Dimethyl-2,6-octadien-1-olChEBI
(e)-GeraniolChEBI
(e)-NerolChEBI
2-trans-3,7-Dimethyl-2,6-octadien-1-olChEBI
3,7-Dimethyl-trans-2,6-octadien-1-olChEBI
Geranyl alcoholChEBI
LemonolChEBI
t-GeraniolChEBI
trans-3,7-Dimethyl-2,6-octadien-1-olChEBI
trans-GeraniolChEBI
b-GeraniolGenerator
Β-geraniolGenerator
(2E)-3,7-Dimethylocta-2,6-dien-1-olHMDB
2-trans-3,7-Dimethyl-2,6-octadiene-1-olHMDB
2E-GeraniolHMDB
3,7-Dimethyl-(2E)-2,6-octadien-1-olHMDB
3,7-Dimethyl-(e)-2,6-octadien-1-olHMDB
FEMA 2507HMDB
GeraniolHMDB
trans-2,6-Dimethyl-2,6-octadien-8-olHMDB
trans-3,7-Dimethy- octa-2,6-dien-1-olHMDB
Geraniol, (Z)-isomerMeSH
Geraniol, 1-(14)C-labeled, (e)-isomerMeSH
NerolMeSH
Geraniol, 2-(14)C-labeled, (e)-isomerMeSH
Geraniol, titanium (4+) saltMeSH
Geraniol, (e)-isomerMeSH
(E)-3,7-Dimethyl-2,6-octadienolPhytoBank
trans-1-Hydroxy-3,7-dimethyl-2,6-octadienePhytoBank
beta-GeraniolPhytoBank
Chemical FormulaC10H18O
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
IUPAC Name(2E)-3,7-dimethylocta-2,6-dien-1-ol
Traditional Namegeraniol
CAS Registry Number106-24-1
SMILES
CC(C)=CCC\C(C)=C\CO
InChI Identifier
InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+
InChI KeyGLZPCOQZEFWAFX-JXMROGBWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
Substituents
  • Acyclic monoterpenoid
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point< -15 °CNot Available
Boiling Point229.00 to 230.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.1 mg/mL at 25 °CNot Available
LogP3.56Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.37 g/LALOGPS
logP2.89ALOGPS
logP2.5ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)16.33ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.18 m³·mol⁻¹ChemAxon
Polarizability19.67 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.66831661259
DarkChem[M-H]-132.78631661259
DeepCCS[M+H]+138.05530932474
DeepCCS[M-H]-134.48630932474
DeepCCS[M-2H]-171.69630932474
DeepCCS[M+Na]+147.09730932474
AllCCS[M+H]+136.732859911
AllCCS[M+H-H2O]+132.732859911
AllCCS[M+NH4]+140.532859911
AllCCS[M+Na]+141.632859911
AllCCS[M-H]-137.732859911
AllCCS[M+Na-2H]-139.732859911
AllCCS[M+HCOO]-142.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
beta-GeraniolCC(C)=CCC\C(C)=C\CO1835.5Standard polar33892256
beta-GeraniolCC(C)=CCC\C(C)=C\CO1226.4Standard non polar33892256
beta-GeraniolCC(C)=CCC\C(C)=C\CO1249.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
beta-Geraniol,1TMS,isomer #1CC(C)=CCC/C(C)=C/CO[Si](C)(C)C1341.9Semi standard non polar33892256
beta-Geraniol,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CO[Si](C)(C)C(C)(C)C1559.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - beta-Geraniol GC-MS (1 TMS)splash10-002f-9800000000-16b748da465c428492a42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Geraniol EI-B (Non-derivatized)splash10-014l-9000000000-25934c23f4bc9ba871422017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Geraniol EI-B (Non-derivatized)splash10-014i-9000000000-a4d79e7813b94cf0d54b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Geraniol EI-B (Non-derivatized)splash10-014i-9100000000-3a5359aae818f9966cbd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Geraniol EI-B (Non-derivatized)splash10-00kf-9200000000-4a8a23071f388f4464512017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Geraniol EI-B (Non-derivatized)splash10-014i-9100000000-f24e92e3c3efdc35a6062017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Geraniol EI-B (Non-derivatized)splash10-014i-9100000000-d8e4f64753ef594f6d402017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Geraniol EI-B (Non-derivatized)splash10-014l-9000000000-2bce8c0905dd12aa5dac2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Geraniol GC-MS (Non-derivatized)splash10-002f-9800000000-16b748da465c428492a42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Geraniol GC-EI-TOF (Non-derivatized)splash10-0006-4900000000-7e43c8601ed65028cae52017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Geraniol GC-MS (Non-derivatized) - 70eV, Positivesplash10-014u-9300000000-c85bc4c928fbf7d824e82016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Geraniol GC-MS (1 TMS) - 70eV, Positivesplash10-030c-9520000000-69b7fbbb25764f7b612e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Geraniol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Geraniol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-014l-9100000000-f59382e51acd0b5402042014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol n/a 10V, negative-QTOFsplash10-0a4i-1900000000-710389d2548f45d605022020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol QTOF 4V, positive-QTOFsplash10-001r-9500000000-d864036a8f8b4cdb20ae2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol QTOF 5V, positive-QTOFsplash10-001r-9400000000-e3661fd0b608943d6b6c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol QTOF 7V, positive-QTOFsplash10-001i-9200000000-d748b4cd92b7c69ffee32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol QTOF 10V, positive-QTOFsplash10-001i-9100000000-b6abc8d3af3aa99879b42020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol QTOF 15V, positive-QTOFsplash10-001i-9000000000-710e0ba546f9b86b8e402020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol QTOF 17V, positive-QTOFsplash10-001i-9000000000-4cc179896d05162706592020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol QTOF 20V, positive-QTOFsplash10-001i-9000000000-7f3a48636d9da2cda8212020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol QTOF 23V, positive-QTOFsplash10-001i-9000000000-4b196d3d8e84ecd0e9f32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol QTOF 25V, positive-QTOFsplash10-003r-9000000000-718f1d4e975f4b2446d12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol QTOF 27V, positive-QTOFsplash10-003u-9000000000-2e43acc8a377504a43292020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol QTOF 30V, positive-QTOFsplash10-005c-9000000000-fe7ffaf2c7e121c33b7c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol QTOF 33V, positive-QTOFsplash10-005c-9000000000-467c307d1f0822b86ea02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol QTOF 35V, positive-QTOFsplash10-005c-9000000000-5939202301ea6107df2c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol QTOF 40V, positive-QTOFsplash10-002f-9000000000-0e13687577d30f6265cc2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol QTOF 45V, positive-QTOFsplash10-0f96-9000000000-e478c8b2587c1134117d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol Orbitrap 1V, positive-QTOFsplash10-000i-1900000000-5f3fc91bdf843e40a2662020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol Orbitrap 1V, positive-QTOFsplash10-000i-1900000000-ab16b7d86a06d659d4f32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Geraniol Orbitrap 2V, positive-QTOFsplash10-000i-3900000000-4dd10bbea41237cba5352020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Geraniol 10V, Positive-QTOFsplash10-0a4r-1900000000-3d437630e5bec67a7e072016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Geraniol 20V, Positive-QTOFsplash10-052r-8900000000-0e505c85cec6344cab5c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Geraniol 40V, Positive-QTOFsplash10-0gb9-9100000000-c7400df359a9559bd5942016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Geraniol 10V, Negative-QTOFsplash10-0udi-0900000000-113756054eed13d33ee42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Geraniol 20V, Negative-QTOFsplash10-0fk9-0900000000-dea43b41c5b791cef9d22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Geraniol 40V, Negative-QTOFsplash10-0aou-9800000000-c028a2bd6550260942512016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013792
KNApSAcK IDC00000845
Chemspider ID13849989
KEGG Compound IDC01500
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGeraniol
METLIN IDNot Available
PubChem Compound637566
PDB IDNot Available
ChEBI ID17447
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1006992
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  6. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  7. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.